N,N′-Bis(3-phenyl­allyl­idene)biphenyl-2,2′-diamine

Dehghanpour, S.; Afshariazar, F.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536809000804

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o307

doi:10.1107/S1600536809000804

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N,N′-Bis(3-phenylallylidene)biphenyl-2,2′-diamine

Saeed Dehghanpour,^a ^* Farzaneh Afshariazar,^a Shan Gao ^b and Seik Weng Ng ^c

^aDepartment of Chemistry, Alzahra University, Vanak, Tehran, Iran, ^bSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: dehganpour_farasha@yahoo.com

(Received 7 January 2009; accepted 7 January 2009; online 14 January 2009)

In the title Schiff base, C₃₀H₂₄N₂, the complete molecule is generated by a crystallographic twofold axis; the aromatic rings of the biphenyl unit are twisted by 60.78 (1)°. The imine double bond has a trans configuration.

Related literature

For a list of the crystal structures of Schiff bases formed by condensing biphenyl-2,2′-diamine with aldehydes or ketones, see: Dehghanpour et al. (2009 ).

Experimental

Crystal data

C₃₀H₂₄N₂
M_r = 412.51
Orthorhombic, F d d 2
a = 15.4354 (12) Å
b = 31.783 (2) Å
c = 9.6188 (8) Å
V = 4718.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 (2) K
0.27 × 0.21 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.982, T_max = 0.989
11331 measured reflections
1427 independent reflections
1021 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.110
S = 1.07
1427 reflections
145 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000804/bt2848sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000804/bt2848Isup2.hkl

checkCIF report

Related literature top

For a list of the crystal structures of Schiff bases formed by condensing biphenyl-2,2'-diamine with aldehydes or ketones, see: Dehghanpour et al. (2009).

Experimental top

Biphenyl-2,2'-diamine (5 mmol) and cinnamaldehyde (10 mmol) were dissolved in diethyl ether (50 ml). The mixture was stirred for 30 min. Evaporation of the solvent gave a solid that was recrystallized from ethanol twice. Yield: 80%. CH&N elemental analysis. Calculated for C₃₀H₂₄N₂: C 87.35, H 5.86, N 6.79%; found: C 87.30, H 5.81, N 9.82%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001); displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. (Symmetry code i: -x, -y, z).

N,N'-Bis(3-phenylallylidene)biphenyl-2,2'-diamine top

Crystal data top

C₃₀H₂₄N₂	F(000) = 1744
M_r = 412.51	D_x = 1.161 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 7049 reflections
a = 15.4354 (12) Å	θ = 3.2–27.5°
b = 31.783 (2) Å	µ = 0.07 mm⁻¹
c = 9.6188 (8) Å	T = 295 K
V = 4718.8 (6) Å³	Cuboid, light yellow
Z = 8	0.27 × 0.21 × 0.16 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	1427 independent reflections
Radiation source: fine-focus sealed tube	1021 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −20→19
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −41→41
T_min = 0.982, T_max = 0.989	l = −12→12
11331 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0608P)² + 0.8672P] where P = (F_o² + 2F_c²)/3
1427 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.11 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₃₀H₂₄N₂	V = 4718.8 (6) Å³
M_r = 412.51	Z = 8
Orthorhombic, Fdd2	Mo Kα radiation
a = 15.4354 (12) Å	µ = 0.07 mm⁻¹
b = 31.783 (2) Å	T = 295 K
c = 9.6188 (8) Å	0.27 × 0.21 × 0.16 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	1427 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1021 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.989	R_int = 0.029
11331 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.110	H-atom parameters constrained
S = 1.07	Δρ_max = 0.11 e Å⁻³
1427 reflections	Δρ_min = −0.15 e Å⁻³
145 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.01193 (13)	0.05064 (6)	0.5676 (2)	0.0523 (5)
C2	−0.02328 (13)	0.02045 (6)	0.4634 (2)	0.0541 (5)
C3	−0.07746 (15)	0.02974 (7)	0.3523 (3)	0.0641 (6)
H3A	−0.0859	0.0097	0.2831	0.077*
C4	−0.11943 (16)	0.06833 (8)	0.3424 (3)	0.0724 (7)
H4A	−0.1561	0.0739	0.2679	0.087*
C5	−0.10622 (16)	0.09796 (7)	0.4433 (3)	0.0695 (7)
H5A	−0.1333	0.1240	0.4363	0.083*
C6	−0.05334 (14)	0.08962 (6)	0.5546 (3)	0.0609 (6)
H6A	−0.0449	0.1101	0.6223	0.073*
C7	0.03355 (16)	0.05664 (7)	0.7976 (3)	0.0598 (6)
H7A	−0.0185	0.0702	0.8165	0.072*
C8	0.09664 (17)	0.05217 (7)	0.9066 (3)	0.0629 (6)
H8A	0.1467	0.0370	0.8870	0.075*
C9	0.08822 (15)	0.06818 (7)	1.0333 (3)	0.0637 (6)
H9A	0.0374	0.0829	1.0516	0.076*
C10	0.15066 (15)	0.06500 (7)	1.1471 (3)	0.0588 (6)
C11	0.22801 (16)	0.04272 (7)	1.1346 (3)	0.0669 (6)
H11A	0.2417	0.0301	1.0502	0.080*
C12	0.28461 (18)	0.03901 (9)	1.2443 (3)	0.0771 (8)
H12A	0.3361	0.0241	1.2337	0.093*
C13	0.2651 (2)	0.05718 (9)	1.3688 (3)	0.0822 (8)
H13A	0.3033	0.0547	1.4431	0.099*
C14	0.18916 (19)	0.07916 (10)	1.3845 (3)	0.0829 (8)
H14A	0.1758	0.0913	1.4697	0.099*
C15	0.13291 (17)	0.08318 (8)	1.2745 (3)	0.0703 (7)
H15A	0.0820	0.0984	1.2860	0.084*
N1	0.04738 (12)	0.04246 (5)	0.6758 (2)	0.0584 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0562 (11)	0.0430 (9)	0.0576 (14)	0.0011 (8)	0.0025 (11)	0.0017 (9)
C2	0.0626 (11)	0.0412 (10)	0.0584 (14)	0.0000 (9)	0.0012 (11)	0.0017 (9)
C3	0.0792 (15)	0.0510 (11)	0.0622 (15)	0.0019 (11)	−0.0095 (13)	−0.0006 (11)
C4	0.0809 (15)	0.0638 (13)	0.0725 (16)	0.0109 (12)	−0.0124 (14)	0.0089 (12)
C5	0.0807 (15)	0.0509 (11)	0.0770 (18)	0.0140 (11)	0.0009 (15)	0.0072 (12)
C6	0.0714 (13)	0.0432 (9)	0.0681 (15)	0.0043 (9)	0.0024 (13)	−0.0018 (10)
C7	0.0649 (13)	0.0496 (11)	0.0648 (16)	−0.0036 (10)	−0.0008 (13)	0.0007 (11)
C8	0.0707 (14)	0.0538 (11)	0.0641 (16)	0.0005 (10)	−0.0006 (12)	−0.0019 (12)
C9	0.0645 (13)	0.0638 (13)	0.0627 (16)	0.0013 (11)	0.0043 (13)	−0.0040 (12)
C10	0.0632 (13)	0.0539 (11)	0.0593 (14)	−0.0054 (10)	0.0053 (12)	−0.0010 (10)
C11	0.0663 (14)	0.0743 (14)	0.0600 (16)	0.0005 (11)	0.0086 (12)	0.0008 (12)
C12	0.0688 (15)	0.0864 (18)	0.076 (2)	0.0019 (13)	0.0035 (14)	0.0137 (15)
C13	0.0814 (17)	0.0908 (19)	0.074 (2)	−0.0112 (15)	−0.0109 (17)	0.0062 (16)
C14	0.100 (2)	0.0861 (17)	0.0621 (18)	−0.0064 (16)	−0.0005 (17)	−0.0145 (15)
C15	0.0763 (15)	0.0673 (13)	0.0673 (17)	0.0006 (12)	0.0044 (14)	−0.0112 (13)
N1	0.0707 (11)	0.0445 (8)	0.0599 (13)	0.0019 (8)	−0.0044 (10)	−0.0029 (9)

Geometric parameters (Å, º) top

C1—C2	1.399 (3)	C8—C9	1.327 (4)
C1—C6	1.400 (3)	C8—H8A	0.9300
C1—N1	1.410 (3)	C9—C10	1.461 (3)
C2—C3	1.389 (3)	C9—H9A	0.9300
C2—C2ⁱ	1.485 (4)	C10—C15	1.383 (4)
C3—C4	1.390 (3)	C10—C11	1.393 (3)
C3—H3A	0.9300	C11—C12	1.375 (4)
C4—C5	1.368 (4)	C11—H11A	0.9300
C4—H4A	0.9300	C12—C13	1.362 (4)
C5—C6	1.373 (4)	C12—H12A	0.9300
C5—H5A	0.9300	C13—C14	1.373 (4)
C6—H6A	0.9300	C13—H13A	0.9300
C7—N1	1.273 (3)	C14—C15	1.375 (4)
C7—C8	1.438 (4)	C14—H14A	0.9300
C7—H7A	0.9300	C15—H15A	0.9300

C2—C1—C6	119.1 (2)	C7—C8—H8A	117.8
C2—C1—N1	118.93 (17)	C8—C9—C10	126.6 (2)
C6—C1—N1	121.7 (2)	C8—C9—H9A	116.7
C3—C2—C1	118.76 (18)	C10—C9—H9A	116.7
C3—C2—C2ⁱ	118.52 (15)	C15—C10—C11	117.3 (2)
C1—C2—C2ⁱ	122.67 (16)	C15—C10—C9	120.3 (2)
C2—C3—C4	121.4 (2)	C11—C10—C9	122.4 (2)
C2—C3—H3A	119.3	C12—C11—C10	121.5 (3)
C4—C3—H3A	119.3	C12—C11—H11A	119.3
C5—C4—C3	119.3 (3)	C10—C11—H11A	119.3
C5—C4—H4A	120.4	C13—C12—C11	119.8 (3)
C3—C4—H4A	120.4	C13—C12—H12A	120.1
C4—C5—C6	120.6 (2)	C11—C12—H12A	120.1
C4—C5—H5A	119.7	C12—C13—C14	120.1 (3)
C6—C5—H5A	119.7	C12—C13—H13A	120.0
C5—C6—C1	120.8 (2)	C14—C13—H13A	120.0
C5—C6—H6A	119.6	C13—C14—C15	120.1 (3)
C1—C6—H6A	119.6	C13—C14—H14A	119.9
N1—C7—C8	121.5 (2)	C15—C14—H14A	119.9
N1—C7—H7A	119.3	C14—C15—C10	121.2 (2)
C8—C7—H7A	119.3	C14—C15—H15A	119.4
C9—C8—C7	124.4 (2)	C10—C15—H15A	119.4
C9—C8—H8A	117.8	C7—N1—C1	120.32 (19)

C6—C1—C2—C3	−1.9 (3)	C8—C9—C10—C15	−179.7 (2)
N1—C1—C2—C3	−175.9 (2)	C8—C9—C10—C11	−2.0 (4)
C6—C1—C2—C2ⁱ	175.3 (2)	C15—C10—C11—C12	−0.2 (4)
N1—C1—C2—C2ⁱ	1.4 (3)	C9—C10—C11—C12	−177.9 (2)
C1—C2—C3—C4	0.7 (3)	C10—C11—C12—C13	0.4 (4)
C2ⁱ—C2—C3—C4	−176.6 (2)	C11—C12—C13—C14	0.0 (5)
C2—C3—C4—C5	0.8 (4)	C12—C13—C14—C15	−0.5 (5)
C3—C4—C5—C6	−1.1 (4)	C13—C14—C15—C10	0.7 (5)
C4—C5—C6—C1	−0.1 (4)	C11—C10—C15—C14	−0.4 (4)
C2—C1—C6—C5	1.7 (3)	C9—C10—C15—C14	177.4 (2)
N1—C1—C6—C5	175.4 (2)	C8—C7—N1—C1	−174.1 (2)
N1—C7—C8—C9	176.2 (2)	C2—C1—N1—C7	−147.5 (2)
C7—C8—C9—C10	−179.2 (2)	C6—C1—N1—C7	38.7 (3)

Symmetry code: (i) −x, −y, z.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₄N₂
M_r	412.51
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	295
a, b, c (Å)	15.4354 (12), 31.783 (2), 9.6188 (8)
V (Å³)	4718.8 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.27 × 0.21 × 0.16

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.982, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	11331, 1427, 1021
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.110, 1.07
No. of reflections	1427
No. of parameters	145
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.15

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the Alzahra University Research Council and Natural Resources, and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
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